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NASCAR Classics: Races to watch before Chicago

View these NASCAR Classics from Chicago and other venues as the Cup Series prepares for the Grant Park 165 on Sunday (4:30 p.m. ET, NBC).

Throughout the 2024 NASCAR season, Ken Martin, director of historical content for the sanctioning body, will offer his suggestions on which historical races fans should watch from the NASCAR Classics library in preparation for each upcoming race weekend.

Martin has worked exclusively for NASCAR since 2008 but has been involved with the sport since 1982, overseeing various projects. He has worked in the broadcast booth for hundreds of races, assisting the broadcast team with different tasks. This includes calculating the “points as they run” for the historic 1992 finale, the Hooters 500 at Atlanta Motor Speedway.

The following suggestions are Ken‘s picks to watch before this Sunday’s Grant Park 165 at the Chicago Street Course (4:30 p.m. ET, NBC, MRN Radio, SiriusXM NASCAR Radio, NBC Sports App).

Shane van Gisbergen stands atop his No. 91 Trackhouse Racing Chevrolet in Victory Lane as his pit crew celebrates around him following his 2023 Chicago Street Race victory.

2023 Grant Park 165 at Chicago Street Course:

The inaugural race on the Chicago Street Course had a little bit of everything as drivers had to face multiple obstacles they were not normally used to while simultaneously chasing the checkered flag.

Rain delayed the start of the hyped-up event for almost two hours. Once the green flag finally waved, fans needed two hands to count how many drivers went off the track or ran into a barrier over the first few laps.

From Brad Keselowski and Kyle Busch to Denny Hamlin and Erik Jones, it was almost a case of who didn‘t have an issue at the start of the race.

Quite possibly the biggest story besides the new course itself was Trackhouse Racing‘s Project 91 car driven by three-time Supercars champion Shane van Gisbergen.

The Auckland, New Zealand driver put the No. 91 car third in qualifying, just behind Hamlin and his driver, Tyler Reddick.

As the race quickly progressed past its weather issues, NASCAR shortened it from 100 to 75 laps, shuffling the strategy of the entire field.

This put van Gisbergen and others at the front of the field, and it was enough as he took the checkered flag in his first career NASCAR race.

Justin Haley, Chase Elliott, Kyle Larson and Busch rounded out the rest of the top-five finishers.

Chase Elliott stands atop his No. 9 Hendrick Motorsports Chevrolet and waves the checkered flag to the crowd following his NASCAR Cup Series victory at Road America.

2021 Jockey Made in America 250 Presented by Kwik Trip at Road America:

The week of July 4th, normally reserved for the traditional race at Daytona International Speedway, saw the Cup Series race at Road America for the first time since 1965.

It wasn‘t the first time a NASCAR national series raced through the twists and turns of Wisconsin since that lone race 65 years beforehand. The Xfinity Series had raced at the track since 2010, with most drivers in the Cup Series field hoisting some type of experience at the track.

The story of the day was reigning series champion Chase Elliott and his Hendrick Motorsports organization. He was relegated to a 34th-place starting position following two separate caution flags while he was out for qualifying.

Elliott worked his way through the field to lead 24 laps and captured his second Cup victory of the season. It was the seventh victory over the previous eight races for Hendrick Motorsports and the 10th victory for the team over the season‘s 20 races.

He outlasted Christopher Bell, Kyle Busch, Kurt Busch and Denny Hamlin for the victory.

Kyle and Chase Briscoe, who finished sixth, each also worked their way through the field for a great finish. Busch started last in 40th, while Briscoe rolled through the field from 35th.

A general view of NASCAR Cup Series cars racing during the inaugural running at Chicagoland Speedway with signage in the background.

2001 Tropicana 400 at Chicagoland Speedway:

The inaugural trip to the brand-new Chicagoland Speedway in Joliet, Illinois, saw the Haas-Carter Motorsports teammates of Todd Bodine and Jimmy Spencer capture the front-row for the event in qualifying.

Four rookies in the field also had solid qualifying showings as Kevin Harvick, Andy Houston, Jason Leffler and Ron Hornaday Jr. all qualified in the first 16 positions.

As the laps dwindled down, it appeared that drivers and their crew chiefs were set up for a fuel mileage battle for the victory. That was until the caution came out for a cut tire from Jeff Burton‘s No. 99 Ford.

Harvick, who led the most laps on the day, was shuffled back to seventh after several drivers stayed out instead of pitting.

However, the fast GM Goodwrench Chevrolet was back out front in less than 10 laps and sailed to his second-career victory.

Robert Pressley came home second behind Harvick, while the Robert Yates Racing cars of Ricky Rudd and Dale Jarrett followed.

The series standings were shuffled as Jarrett and Jeff Gordon left the race tied for first in the standings, with Rudd just 18 points behind.